EP0530648A2 - Verträgliche Polyestermischungen - Google Patents

Verträgliche Polyestermischungen Download PDF

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Publication number
EP0530648A2
EP0530648A2 EP92114466A EP92114466A EP0530648A2 EP 0530648 A2 EP0530648 A2 EP 0530648A2 EP 92114466 A EP92114466 A EP 92114466A EP 92114466 A EP92114466 A EP 92114466A EP 0530648 A2 EP0530648 A2 EP 0530648A2
Authority
EP
European Patent Office
Prior art keywords
polymer
compatibilizer
vinylphenol
repeating units
previous
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP92114466A
Other languages
English (en)
French (fr)
Other versions
EP0530648A3 (en
Inventor
Ralph Hayes c/o EASTMAN KODAK COMPANY Colby
Christine J.T. c/o EASTMAN KODAK COMPANY Landry
Michael Raymond c/o EASTMAN KODAK COMPANY Landry
Timothy Edward c/o EASTMAN KODAK COMPANY Long
Dennis Jon c/o EASTMAN KODAK COMPANY Massa
David M. c/o EASTMAN KODAK COMPANY Teegarden
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Chemical Co
Original Assignee
Eastman Kodak Co
Eastman Chemical Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co, Eastman Chemical Co filed Critical Eastman Kodak Co
Publication of EP0530648A2 publication Critical patent/EP0530648A2/de
Publication of EP0530648A3 publication Critical patent/EP0530648A3/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides

Definitions

  • the present invention is directed to blends of certain polymers.
  • the blends are compatible and find many uses such as packaging applications owing to their chemical resistance and toughness.
  • Polymer blends are a route to novel and useful materials having improved properties, such as easier processing, better mechanical properties, chemical resistance and lower cost.
  • blend physical properties may be poor.
  • a compatibilizer whose purpose it is to improve the blend properties.
  • Compatibilizers are typically either random, graft, or block copolymers. Reference is also made to United States Patents 4,885,334 and 4,886,126 for compositions of this general type.
  • a compatibilizer in admixture with a blend of a polyphenylene oxide polymer and a styrene acrylonitrile polymer.
  • the compatibilizer is a block copolymer of styrene and acrylonitrile.
  • Block copolymer compatibilizers for a blend of polyphenylene oxides and a "polar thermoplastic resin", which can be a polyester, are described in United States Patent 4,885,334.
  • the compatibilizer is a modified block copolymer obtained by subjecting a hydrogenated block copolymer comprising an aromatic vinyl compound polymer block (for example, derived from styrene) and a conjugated diene compound polymer block (for example, 1,3, butadiene) to graft polymerization in the presence of a monomer having an epoxy group (for example, glycidyl methacrylate).
  • a hydrogenated block copolymer comprising an aromatic vinyl compound polymer block (for example, derived from styrene) and a conjugated diene compound polymer block (for example, 1,3, butadiene) to graft polymerization in the presence of a monomer having an epoxy group (for example, glycidyl methacrylate).
  • blends of certain polyesters with phenylene oxide containing polymers have brittle mechanical properties.
  • a compatibilizer that, when added to these blends, improves their mechanical properties and allows the potential advantages of these blends--for example, easier processing than phenylene oxide containing polymers, higher thermal dimensional stability than the polyesters alone, and lower cost than phenylene oxide containing polymers--to be realized.
  • a polymer blend composition comprising a polymer that is miscible with polystrene and a thermoplastic polyester wherein the diacid component of said polyester includes aromatic groups and wherein the diol component comprises at least 20 percent by weight of a noncyclic, aliphatic diol, said blend further comprising a copolymer compatibilizer in an amount sufficient to effect compatibility between said polyphenylene ether containing polymer and said polyester, said compatibilizer comprising a copolymer having repeating units derived from an aromatic vinyl compound monomer and a vinylphenol monomer.
  • One component of the blend of the invention is a polymer that is miscible with polystyrene, such as polyphenylene oxide (IV).
  • polystyrene such as polyphenylene oxide (IV).
  • IV polyphenylene oxide
  • Useful polyphenylene ether containing polymers are described, for example in the above referenced U.S. Patent 4,885,334 at Col. 1-Col. 2. These polymers are obtained by the polycondensation of one or a mixture of phenols represented by the formula: wherein R1 represents a lower alkyl group having from 1 to 3 carbon atoms and R2 and R3 each independently represent a hydrogen atom or a lower alkyl group having from 1 to 3 carbon atoms.
  • polystyrene examples include polystyrene, high-impact polystyrene, tetramethylbisphenol-A polycarbonate, poly(vinyl methyl ether), and blends of polyphenylene ethers with polystyrene, and styrene-containing copolymers.
  • One of the components of the blend of the present invention is a thermoplastic polyester wherein the diacid component of the polyester includes aromatic groups and wherein the diol component of the polyester comprises at least 20 mole percent of a non-cyclic, aliphatic diol.
  • the diacid component will be considered to be aromatic if at least 50 mole percent of the diacid is aromatic.
  • mixtures of diacids can be used.
  • Particularly useful diacid components result in repeating units represented by the formula: wherein a is an integer of from 1 to 4 and each R4 is independently selected from the group consisting of hydrogen; alkyl groups having from 1 to 4 carbon atoms, for example methyl, ethyl and t-butyl; and halogen, particularly bromo and chloro.
  • Particularly useful diacid components are derived from acids which include: phthalic acid; isophthalic acid; terephthalic and naphthoic acid.
  • the second component of the polyester is a non-cyclic diol component.
  • the diol component can include up to 80 mole percent of a cyclic component.
  • Useful diol components result in repeating units having the structure: wherein R5 represents a straight or branched alkylene group of from 1 to 10 carbon atoms, for example, ethyl, butyl and neopentyl.
  • diols which can be used up to 80 mole percent include cyclic diols resulting in repeating units having the formula: wherein n is 0 to 2 and a is an integer from 1 to 4 and each R4 is independently selected from the group consisting of hydrogen; alkyl groups having from 1 to 4 carbon atoms, for example methyl, ethyl and t-butyl; and halogen, particularly bromo and chloro.
  • n is an integer from 2 to 4 and m is an integer from 2 to 15.
  • diol components are derived from diols which include: ethylene glycol, butanediol, cyclohexylene dimethanol, 1,2-propanediol and neopentyl glycol.
  • miscible it is meant that the blended polymers form a homogeneous blend that has a single glass transition temperature.
  • amorphous miscible blends are clear. In a typical test for clarity a blend of interest is coated or cast into a thin film. A blend is considered to be clear if ordinary newsprint can be read through the film. Immiscible blends are those that have more than one glass transition temperature or are opaque or show two distinct solid state NMR relaxation times.
  • the term compatible is a more general term typically meaning that the components mix and process without difficulty and have good material properties.
  • polyesters that are useful in the invention can be made by methods which are extremely well known in the art. In fact, many of the useful polyesters are commercially available. Useful polyesters are commercially available from the Eastman Kodak Company under the trade names TENITE®, KODAK KODAPAK®, EKTAR PCTG® and EKTAR HPETG®.
  • the blend of the invention further comprises a compatibilizer.
  • the compatibilizer is a copolymer having repeating units derived from an aromatic vinyl compound monomer and a vinylphenol monomer.
  • the aromatic vinyl compound monomer can be represented by the formula: wherein R6 and R7 are independently selected from the group consisting of a hydrogen atom, a lower alkyl group having from 1 to 6 carbon atoms, a chlorine atom and a bromine atom.
  • Useful vinyl aromatic monomers include styrene, p-methylstyrene, ⁇ -methylstyrene, t-butylstyrene and copolymers.
  • the currently preferred monomer is styrene because it is inexpensive and readily available.
  • the other component of the compatibilizer useful in the invention is a poly(vinylphenol).
  • These polymers include repeating units derived from vinylphenol or derivatives thereof.
  • Useful repeating units are derived from vinylphenol or derivatives of vinylphenol where the hydrogen of the hydroxy group is replaced with a group such as metal ions, silyl or organic groups such as tertiary-butyloxycarbonyloxy (tBOC), alkyl, alkanoyl, and benzoyl.
  • repeating units can be represented by the formula: wherein R8 is hydrogen or methyl and R9 is selected from the group consisting of -OH, -OSi(R10)3 and -OM where M is a metal cation, tBOC, OR10 and OCOR10, where R10 is selected from alkyl groups having 1 to 5 carbon atoms or aryl.
  • M can be any univalent or divalent alkali, alkaline earth or transition metal cation. Non-limiting examples of such cations include sodium, magnesium, calcium, lithium, potassium and zinc cations.
  • the group is not a hydroxy group, it is preferred to convert it to a hydroxy group. That is, the other alternatives to phenol itself are precursors to vinylphenol containing polymers.
  • R9 in the formula above can be located in either the para- or meta- position. It is preferred, primarily for reasons of availability of starting materials and ease of synthesis, that R9 be located in the para- position. Additionally, it is contemplated that, in addition to the R9 substituent, the pendant benzene ring can be substituted with such non-interfering substituents as C1-C4 alkyl, or halogen in one or both meta positions.
  • the styrene-vinylphenol block copolymer compatibilizers can be prepared by the method of Nakahama disclosed in Yuki Gosei Kagaku Vol. 47, pp. 448-456 (1989); American Chemical Society Polymer Preprints , Vol 27, No. 1, pp. 194-5 (1986); and Japanese Kokai 59-53509 (1984).
  • Graft copolymer compatibilizers can be prepared by conventional free radical copolymerization of a methacryl-terminated polystyrene macromonomer and a suitably protected vinylphenol monomer.
  • Poly(vinylphenol) homopolymer and random copolymers(III) can also be prepared by conventional free radical polymerization.
  • the preferred range for the molecular weight of the vinylphenol containing copolymer is between 1,500 and 500,000. Particularly preferred are vinylphenol polymers having a molecular weight between 20,000 and 250,000.
  • the preparation of high molecular weight vinylphenol containing polymers is described in: Frechet and others; NOVEL DERIVATIVES OF POLY(4-HYDROXYSTYRENE) WITH EASILY REMOVABLE TERTIARY, ALLYLIC OR BENZYLIC ETHERS; Polymer Bulletin 20 , 427-434 (1988).
  • thermoplastic blends can be made by methods which are well known in the art. These thermoplastic blends, for example, can be made by mixing powders of the blend components together and then melt extruding the mixture in a screw extruder. In another method, both components are dissolved in a common solvent, for example dioxane, pyridine or tetrahydrofuran, and then precipitated in a non-solvent for both of the polymers, such as for example hexane. In another method, both components are dissolved in a common solvent and solvent cast onto an inert substrate.
  • a common solvent for example dioxane, pyridine or tetrahydrofuran
  • PCTG 5445 An Eastman polyester, EKTAR PCTG® 5445 (hereinafter "PCTG 5445" as described above), was obtained in pellet form, was then ground in a grinder in the presence of liquid nitrogen, and was then forced through a fine-mesh strainer and subsequently dried overnight at 105°C in vacuum.
  • Poly(styrene-b-vinylphenol), (I) prepared by the method of Nakahama (referenced above) was received in powder form, and was dried overnight at 115°C in vacuum.
  • a dry blend was prepared of 9.7 g PCTG 5445, 9.7 g (IV), and 0.85 g (I) by stirring and shaking in a bottle.
  • a film of this blend was then melt extruded at 260°C on a laboratory extruder equipped with a 1/4-in screw and 2-in slit die. Continuous films approximately 2" wide and 0.015" to 0.025" thick were obtained.
  • the same procedure was followed to prepare a 1/1 by weight melt-extruded blend of EKTAR PCTG® 5445 and (IV) without added (I). The process was repeated using compatibilizers II, III and poly(vinylphenol) homopolymer (for comparison).
  • Example 6 Compatibilized 0.25/0.25/0.50 blends of Poly (2,6-dimethyl-1,4-phenylene oxide)/Polystyrene/PCTG 5445.
  • PS molding grade polystyrene
  • Another blend having the same 0.25/0.25/0.5 composition but containing 4.3-wt% poly(styrene- b -vinylphenol) block copolymer compatibilizer (I) was prepared by combining 9.7g of PPO/PS, 9.7g PCTG 5445, and 0.87g poly(styrene- b -vinylphenol) and extruding under the same conditions.
  • the mechanical properties for these blends are reported in Table II and show more than a factor of 10 increase in strain at break and work-to-break (toughness) in the blend having the added block copolymer compatibilizer.
  • TMBPA-PC 10g of TMBPA-PC (as described above) and 10g PCTG 5445 were ground as described in Example 1, mixed, dried in vacuum, and extruded at 276°C.
  • Another blend having the same composition but containing 4.3-wt% poly(styrene- b -vinylphenol) block copolymer compatibilizer was prepared by combining 9.7g of TMBPA-PC, 9.7g PCTG 5445, and 0.87g poly(styrene- b -vinylphenol) and extruding under the same conditions.
  • the mechanical properties for these blends are reported in Table III and show improved strength and toughness (stress at break and work-to-break) in the blend having the added block copolymer compatibilizer.
  • Other examples of the invention are reported in Table III and show improved strength and toughness (stress at break and work-to-break) in the blend having the added block copolymer compatibilizer.
  • Blend Composition Stress at break ⁇ b MPa Strain at break ⁇ b , % Yield stress , ⁇ y , MPa Tensile Modulus, MPa Work to break, w b , MPa 10/90 PPO/PCTG5445 Comparison 24 ⁇ 2 17 ⁇ 22 32 ⁇ 2 1020 ⁇ 70 4 ⁇ 6
  • Example 17 10/90 PPO/PCTG5445 with Graft Compatibilizer a (II) 26 ⁇ 4 62 ⁇ 39 29 ⁇ 6 1080 ⁇ 80 11 ⁇ 5 30/70 PPO/PCT5445 Comparison 34 ⁇ 2 4.4 ⁇ 0.8 36 ⁇ 4 1170 ⁇ 70 1.1 ⁇ 0.3
  • Example 18 30/70 PPO/PCT5445 with Graft Compatibilizer a (II) 30 ⁇ 1 14 ⁇ 7 38 ⁇ 2 1220 ⁇ 70 4 ⁇ 2 50/50 PPO/PCT5445 Comparison 38 ⁇ 3 4.6 ⁇ 0.7 40 ⁇ 3 1280 ⁇ 80 1.1 ⁇ 0.3
  • Example 19 50/50 PPO/PCT5445 with Graft Compatibilizer a (
  • Blend Composition Stress at break ⁇ b MPa Strain at break ⁇ b , % Yield stress , ⁇ y , MPa Tensile Modulus, MPa Work to break, w b , MPa PS/PCTG5445 1/1 Comparison 38 ⁇ 6 3.3 ⁇ 0.4 None 1500 ⁇ 200 0.8 ⁇ 0.2
  • Example 22 PS/PCTG5445/(I) Block a 0.48/0.48/.042 30 ⁇ 5 13 ⁇ 8 40 ⁇ 3 1580 ⁇ 80 4 ⁇ 2 a 36-wt% vinylphenol and 64-wt% polystyrene

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP19920114466 1991-08-26 1992-08-25 Compatible polyester blends Withdrawn EP0530648A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US749812 1991-08-26
US07/749,812 US5276089A (en) 1991-08-26 1991-08-26 Compatible polyester blends

Publications (2)

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EP0530648A2 true EP0530648A2 (de) 1993-03-10
EP0530648A3 EP0530648A3 (en) 1993-03-31

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EP19920114466 Withdrawn EP0530648A3 (en) 1991-08-26 1992-08-25 Compatible polyester blends

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US (1) US5276089A (de)
EP (1) EP0530648A3 (de)
JP (1) JPH05230303A (de)
CA (1) CA2074912A1 (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993024572A1 (en) * 1992-06-01 1993-12-09 Eastman Chemical Company Polyester/polyphenylene ether blends
EP1153981A2 (de) * 2000-05-10 2001-11-14 Bayer Corporation Verträgliche Mischung von Polycarbonat mit Vinyl(co)polymer
US8574694B2 (en) 2009-11-03 2013-11-05 Curwood, Inc. Packaging sheet with improved cutting properties

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3689997B2 (ja) * 1996-08-26 2005-08-31 ブラザー工業株式会社 給紙装置及び印字装置
PL2083999T3 (pl) * 2006-10-16 2011-01-31 Valspar Sourcing Inc Wielowarstwowa folia termoplastyczna
KR100832568B1 (ko) * 2006-11-16 2008-05-27 주식회사 엘지화학 접착성이 우수한 배향막 조성물
US20110104342A1 (en) * 2009-11-03 2011-05-05 Kevin David Glaser Chlorine-Free Packaging Sheet with Tear-Resistance Properties

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0337165A2 (de) * 1988-04-15 1989-10-18 Ge Chemicals, Inc. Zusammensetzungen, auf der Basis von einer Polymermischung, die ein Copolymer als Kompatibilisierungsmittel enthält

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63128069A (ja) * 1986-11-19 1988-05-31 Mitsubishi Petrochem Co Ltd 熱可塑性樹脂組成物
NL8603112A (nl) * 1986-12-08 1988-07-01 Gen Electric Polymeermengsel met polyfenyleenether, polyester en styreen polymeer.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0337165A2 (de) * 1988-04-15 1989-10-18 Ge Chemicals, Inc. Zusammensetzungen, auf der Basis von einer Polymermischung, die ein Copolymer als Kompatibilisierungsmittel enthält

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
POLYMER vol. 26, 1985, pages 228 - 234 E.J. MOSKALA ET AL. 'Concerning the miscibility of poly(vinylphenol) blends FTi.r. study' *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993024572A1 (en) * 1992-06-01 1993-12-09 Eastman Chemical Company Polyester/polyphenylene ether blends
EP1153981A2 (de) * 2000-05-10 2001-11-14 Bayer Corporation Verträgliche Mischung von Polycarbonat mit Vinyl(co)polymer
EP1153981A3 (de) * 2000-05-10 2002-02-27 Bayer Corporation Verträgliche Mischung von Polycarbonat mit Vinyl(co)polymer
US8574694B2 (en) 2009-11-03 2013-11-05 Curwood, Inc. Packaging sheet with improved cutting properties

Also Published As

Publication number Publication date
JPH05230303A (ja) 1993-09-07
EP0530648A3 (en) 1993-03-31
US5276089A (en) 1994-01-04
CA2074912A1 (en) 1993-02-27

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